Boosting Energy-Transfer Processes via Dispersion Interactions

被引:7
作者
Cerveri, Alessandro [1 ]
Scarica, Gabriele [1 ]
Sparascio, Sara [1 ]
Hoch, Matteo [1 ]
Chiminelli, Maurizio [1 ]
Tegoni, Matteo [1 ]
Protti, Stefano [2 ]
Maestri, Giovanni [1 ]
机构
[1] Univ Parma, Dept Chem Life Sci & Environm Sustainabil, Parco Area Sci 17-A, I-43124 Parma, Italy
[2] Univ Pavia, Dept Chem, PhotoGreen Lab, Via Taramelli 10, Pavia, Italy
关键词
Catalysis; Cycloaddition; Energy transfer; pi interactions; Radical reactions; HYDROGEN-ATOM TRANSFER; PHOTOREDOX CATALYSIS; LONDON DISPERSION; COMBINING PHOTOREDOX; POSITIVE CURVATURE; MERGING PHOTOREDOX; DUAL CATALYSIS; ALKENES; PHOTOCATALYSIS; CHEMISTRY;
D O I
10.1002/chem.202304010
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The generation of open-shell intermediates under mild conditions has opened broad synthetic opportunities during this century. However, these reactive species often require a case specific and tailored tuning of experimental parameters in order to efficiently convert substrates into products. We report a general approach that can overcome these ubiquitous limitations for several visible-light promoted energy-transfer processes. The use of either naphthalene (5-20 equiv.) or simple binaphthyl derivatives (10-30 mol %) greatly increases their efficiency, giving rise to a new strategy for catalysis. The trend is consistent among different media, photocatalysts, light sources and substrates, allowing one to improve existing methods, to more easily optimize conditions for new ones, and, moreover, to disclose otherwise inaccessible reaction pathways.
引用
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页数:9
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共 111 条
[1]   Gabedit-A Graphical User Interface for Computational Chemistry Softwares [J].
Allouche, Abdul-Rahman .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2011, 32 (01) :174-182
[2]   Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis [J].
Amos, Stephanie G. E. ;
Garreau, Marion ;
Buzzetti, Luca ;
Waser, Jerome .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 :1163-1187
[3]   Calixarene-based multivalent ligands [J].
Baldini, L. ;
Casnati, A. ;
Sansone, F. ;
Ungaro, R. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) :254-266
[4]   Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model [J].
Barone, V ;
Cossi, M .
JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (11) :1995-2001
[5]   Dissection of the Polar and Non-Polar Contributions to Aromatic Stacking Interactions in Solution [J].
Bravin, Carlo ;
Piekos, Justyna A. ;
Licini, Giulia ;
Hunter, Christopher A. ;
Zonta, Cristiano .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (44) :23871-23877
[6]   Naphthalene in the higher triplet excited state [J].
Cai, XC ;
Hara, M ;
Kawai, K ;
Tojo, S ;
Majima, T .
CHEMICAL COMMUNICATIONS, 2003, (02) :222-223
[7]   Diastereoselective and enantioselective photoredox pinacol coupling promoted by titanium complexes with a red-absorbing organic dye [J].
Calogero, Francesco ;
Magagnano, Giandomenico ;
Potenti, Simone ;
Pasca, Francesco ;
Fermi, Andrea ;
Gualandi, Andrea ;
Ceroni, Paola ;
Bergamini, Giacomo ;
Cozzi, Pier Giorgio .
CHEMICAL SCIENCE, 2022, 13 (20) :5973-5981
[8]   Photoinduced intermolecular hydrogen atom transfer reactions in organic synthesis [J].
Cao, Hui ;
Tang, Xinxin ;
Tang, Haidi ;
Yuan, Ye ;
Wu, Jie .
CHEM CATALYSIS, 2021, 1 (03) :523-598
[9]   High Upconversion Efficiency from Hetero Triplet-Triplet Annihilation in Multiacceptor Systems [J].
Cao, Xian ;
Hu, Bo ;
Zhang, Peng .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2013, 4 (14) :2334-2338
[10]   Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration [J].
Capaldo, Luca ;
Ravelli, Davide ;
Fagnoni, Maurizio .
CHEMICAL REVIEWS, 2022, 122 (02) :1875-1924